Microsoft was once the king of technology, and while they were never "cool," they were the go-to company for your software needs.

So, in order to become "cool," Microsoft once tried to by the Seattle music label Sub Pop. The label famously launched the legendary grunge band Nirvana, and Microsoft, being a Washington-based company, thought they had some leverage in purchasing the label and launching an entertainment side. Microsoft had only offered them $4 million, though, Geffen records offered $8 million and Sony Music $5 million. 

"Bill Gates, who at the time considered himself to be 'the future of entertainment,' couldn't have been a more dull character," said Dana Giacchetto, who brokered deals for the label.

"It definitely would have made Microsoft a bit more hip," says Giacchetto. "Which in hindsight might have actually made Microsoft a player in entertainment. They're still not."

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[via The Guardian]